4-hydroxy-N-(4-hydroxyphenethyl)benzamide | 1173289-26-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 4-hydroxy-N-(4-hydroxyphenethyl)benzamide
• 英文别名: 4-hydroxy-N-[2-(4-hydroxyphenyl)ethyl]benzamide；oretamide
• CAS: 1173289-26-3
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: GZLCCOBLLZQSIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对羟基苯甲酸 在 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-hydroxy-N-(4-hydroxyphenethyl)benzamide
  参考文献：
  名称：

  Protective effects of veskamide, enferamide, becatamide, and oretamide on H2O2-induced apoptosis of PC-12 cells

  摘要：

  Veskamide, enferamide, becatamide. and oretamide are phenolic amides whose analogues are found in plants. In this study, the four amides were prepared by chemical synthesis and their protective effects on H2O2-induced apoptosis in PC-12 cells were investigated. The syntheses were relatively simple and the yields were more than 43%. Using NMR spectroscopic methods, the chemical structures of veskamide, enferamide, becatamide, and oretamide were confirmed. The decreasing order of the protective effects on H2O2-induced apoptosis was becatamide > enferamide >= oretamide > veskamide. In fact, becatamide suppressed H2O2-induced mitochondrial membrane depolarization in a dose-dependent manner. At the concentration of 10 mu M, becatamide maintained mitochondrial membrane depolarization at 16% compared to 51% in H2O2-treated PC-12 cells (P < 0.05). Also, at the same concentration, becatamide inhibited H2O2-induced caspase-9 activation and caspase-independent chromatin condensation by 68% (P < 0.05) and 73% (P < 0.05), respectively. This is the first report about the chemical synthesis of becatamide and its potential biological activity to inhibit H2O2-induced apoptosis of PC-12 cells via protecting mitochondrial membrane integrity, thereby suppressing caspase-9 activation and chromatin condensation. Published by Elsevier GmbH.

  DOI：

  10.1016/j.phymed.2011.01.025

文献信息

• Structure−Activity Relationships and Cancer-Cell Selective Toxicity of Novel Inhibitors of Glioma-Associated Oncogene Homologue 1 (Gli1) Mediated Transcription
  作者：Neeraj Mahindroo、Michele C. Connelly、Chandanamali Punchihewa、Hiromichi Kimura、Matthew P. Smeltzer、Song Wu、Naoaki Fujii

  DOI：10.1021/jm900106f

  日期：2009.7.23

  We report novel inhibitors of Gli1-mediated transcription as potential anticancer agents. Focused chemical libraries were designed and assessed for inhibition of functional cell-based Gli1-mediated transcription and selective toxicity toward cancer cells. The SAR was revealed, and the selectivity of the lead compounds' inhibition of Gli1-mediated transcription over that of Gli2 was determined. Compound 63 (NMDA298-1), which inhibited Gli1-mediated transcription in C3H10T1/2 cells with all IC50 of 6.9 mu M, showed 3-fold selectivity for inhibiting transcription mediated by Gli1 over that by Gli2. Cell-viability assays were performed to evaluate the chemical library in a normal cell line and a panel of cancer cell lines with or without up-regulated expression of the Gli1 gene. These compounds decreased the viability of several cancer cell lines but were less active in the noncancerous BJ-hTERT cells.
• Protective effects of veskamide, enferamide, becatamide, and oretamide on H2O2-induced apoptosis of PC-12 cells
  作者：Jae B. Park

  DOI：10.1016/j.phymed.2011.01.025

  日期：2011.7

  Veskamide, enferamide, becatamide. and oretamide are phenolic amides whose analogues are found in plants. In this study, the four amides were prepared by chemical synthesis and their protective effects on H2O2-induced apoptosis in PC-12 cells were investigated. The syntheses were relatively simple and the yields were more than 43%. Using NMR spectroscopic methods, the chemical structures of veskamide, enferamide, becatamide, and oretamide were confirmed. The decreasing order of the protective effects on H2O2-induced apoptosis was becatamide > enferamide >= oretamide > veskamide. In fact, becatamide suppressed H2O2-induced mitochondrial membrane depolarization in a dose-dependent manner. At the concentration of 10 mu M, becatamide maintained mitochondrial membrane depolarization at 16% compared to 51% in H2O2-treated PC-12 cells (P < 0.05). Also, at the same concentration, becatamide inhibited H2O2-induced caspase-9 activation and caspase-independent chromatin condensation by 68% (P < 0.05) and 73% (P < 0.05), respectively. This is the first report about the chemical synthesis of becatamide and its potential biological activity to inhibit H2O2-induced apoptosis of PC-12 cells via protecting mitochondrial membrane integrity, thereby suppressing caspase-9 activation and chromatin condensation. Published by Elsevier GmbH.